Huang Qinhua, Larock Richard C
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
J Org Chem. 2003 Sep 19;68(19):7342-9. doi: 10.1021/jo034449x.
An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double-bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields.
通过钯催化各种内炔的环化反应，已开发出一种高效合成高度取代萘的方法，该方法在相对温和的反应条件下，一步形成两个新的碳 - 碳键。此方法也已用于咔唑的合成，不过需要更高的反应温度。该过程包括炔烃的芳基钯化反应，接着是分子内Heck烯烃化反应和双键异构化反应。该方法适用于多种官能团，并能以良好至优异的产率得到预期的高度取代萘和咔唑。
